JP4934681B2 - カルボキサミド節足動物駆除物質の液体調合物 - Google Patents
カルボキサミド節足動物駆除物質の液体調合物 Download PDFInfo
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- JP4934681B2 JP4934681B2 JP2008549506A JP2008549506A JP4934681B2 JP 4934681 B2 JP4934681 B2 JP 4934681B2 JP 2008549506 A JP2008549506 A JP 2008549506A JP 2008549506 A JP2008549506 A JP 2008549506A JP 4934681 B2 JP4934681 B2 JP 4934681B2
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- -1 C 3 glycols Chemical class 0.000 claims description 161
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 77
- 150000003857 carboxamides Chemical class 0.000 claims description 64
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- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 claims description 6
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- DSOOGBGKEWZRIH-UHFFFAOYSA-N nereistoxin Chemical class CN(C)C1CSSC1 DSOOGBGKEWZRIH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 108010003516 norsynephrine receptor Proteins 0.000 description 1
- YTYGAJLZOJPJGH-UHFFFAOYSA-N noviflumuron Chemical compound FC1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F YTYGAJLZOJPJGH-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960000321 oxolinic acid Drugs 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000242 pagocytic effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 229960002132 pyrrolnitrin Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 102000042094 ryanodine receptor (TC 1.A.3.1) family Human genes 0.000 description 1
- 108091052345 ryanodine receptor (TC 1.A.3.1) family Proteins 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000009718 spray deposition Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/92—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more halogen atoms as ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
- A01N63/20—Bacteria; Substances produced thereby or obtained therefrom
- A01N63/22—Bacillus
- A01N63/23—B. thuringiensis
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
- A01N63/40—Viruses, e.g. bacteriophages
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Virology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
Description
(a)約0.1〜約40%の少なくとも1つの室温で固体のカルボキサミド節足動物駆除物質;
(b)0〜約20%の少なくとも1つのその他の生物活性物質;
(c)約30〜約95%の少なくとも1つの水不混和性の液体担体;
(d)約0〜約50%の少なくとも1つの乳化剤;
(e)約0.01〜約10%のシリカ増粘剤;
(f)約0.1〜約10%の、水、C1〜C12アルカノール、および、C2〜C3グリコールから選択される少なくとも1つのプロトン性溶媒;および、
(g)約0.001〜約5%の少なくとも1つの水溶性カルボン酸、
を含む。
実施態様1.発明の要約で説明した節足動物を駆除するための懸濁液濃縮組成物において、構成要素(a)(すなわち、少なくとも1つのカルボキサミド節足動物駆除物質)は、以下の式1で示されるアントラニルアミド(また、アントラニル酸ジアミドとしても説明されている)、それらのN−酸化物および塩から選択される:
Xは、N、CF、CCl、CBrまたはCIであり;
R1は、CH3、Cl、BrまたはFであり;
R2は、H、F、Cl、Brまたは−CNであり;
R3は、F、Cl、Br、C1〜C4ハロアルキル、または、C1〜C4ハロアルコキシであり;
R4aは、H、C1〜C4アルキル、シクロプロピルメチル、または、1−シクロプロピルエチルであり;
R4bは、H、または、CH3であり;
R5は、H、F、Cl、または、Brであり;および、
R6は、H、F、Cl、または、Brである。
N−[4−クロロ−2−メチル−6−[[(1−メチルエチル)アミノ]カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミド、
N−[4−クロロ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−N−[4−クロロ−2−メチル−6−[[(1−メチルエチル)アミノ]カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−N−[4−クロロ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミド、
1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(2−クロロフェニル)−N−[4−シアノ−2−メチル−6−[[(1−メチルエチル)アミノ]カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(2−クロロフェニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(2−クロロフェニル)−N−[2,4−ジクロロ−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−N−[4−クロロ−2−[[(シクロプロピルメチル)アミノ]カルボニル]−6−メチルフェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−[[(シクロプロピルメチル)アミノ]カルボニル]−6−メチルフェニル]−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−N−[4−クロロ−2−[[(1−シクロプロピルエチル)アミノ]カルボニル]−6−メチルフェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド、および、
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−[[(1−シクロプロピルエチル)アミノ]カルボニル]−6−メチルフェニル]−1H−ピラゾール−5−カルボキサミド。
R11は、CH3、Cl、BrまたはIであり;
R12は、CH3、または、Clであり;
R13は、C1〜C3フルオロアルキルであり;
R14は、H、または、CH3であり;
R15は、H、または、CH3であり;
R16は、C1〜C2アルキルであり;および、
nは、0、1または2である。
実施態様A.発明の要約で説明した節足動物を駆除するための懸濁液濃縮組成物において、構成要素(a)(すなわち、少なくとも1つのカルボキサミド節足動物駆除物質)は、以下の式1で示されるアントラニルアミド、それらのN−酸化物および塩から選択される:
Xは、N、CF、CCl、CBrまたはCIであり;
R1は、CH3、Cl、BrまたはFであり;
R2は、H、F、Cl、Brまたは−CNであり;
R3は、F、Cl、Br、C1〜C4ハロアルキル、または、C1〜C4ハロアルコキシであり;
R4aは、H、C1〜C4アルキル、シクロプロピルメチル、または、1−シクロプロピルエチルであり;
R4bは、H、または、CH3であり;
R5は、H、F、Cl、または、Brであり;および、
R6は、H、F、Cl、または、Brである。
R11は、CH3、Cl、BrまたはIであり;
R12は、CH3、または、Clであり;
R13は、C1〜C3フルオロアルキルであり;
R14は、H、または、CH3であり;
R15は、H、または、CH3であり;
R16は、C1〜C2アルキルであり;および、
nは、0、1または2である。
Xは、N、CF、CCl、CBrまたはCIであり;
R1は、CH3、Cl、BrまたはFであり;
R2は、H、F、Cl、Brまたは−CNであり;
R3は、F、Cl、Br、C1〜C4ハロアルキル、または、C1〜C4ハロアルコキシであり;
R4aは、H、C1〜C4アルキル、シクロプロピルメチル、または、1−シクロプロピルエチルであり;
R4bは、H、または、CH3であり;
R5は、H、F、Cl、または、Brであり;および、
R6は、H、F、Cl、または、Brである;
R11は、CH3、Cl、BrまたはIであり;
R12は、CH3、または、Clであり;
R13は、C1〜C3フルオロアルキルであり;
R14は、H、または、CH3であり;
R15は、H、または、CH3であり;
R16は、C1〜C2アルキルであり;および、
nは、0、1または2である。
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−N−[4−クロロ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド、
N−[4−クロロ−2−メチル−6−[[(1−メチルエチル)アミノ]カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミド、
N−[4−クロロ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−N−[4−クロロ−2−メチル−6−[[(1−メチルエチル)アミノ]カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド、
1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(2−クロロフェニル)−N−[4−シアノ−2−メチル−6−[[(1−メチルエチル)アミノ]カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(2−クロロフェニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(2−クロロフェニル)−N−[2、4−ジクロロ−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−N−[4−クロロ−2−[[(シクロプロピルメチル)アミノ]カルボニル]−6−メチルフェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−[[(シクロプロピルメチル)アミノ]−カルボニル]−6−メチルフェニル]−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−N−[4−クロロ−2−[[(1−シクロプロピルエチル)アミノ]カルボニル]−6−メチルフェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド、
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−[[(1−シクロプロピルエチル)アミノ]カルボニル]−6−メチルフェニル]−1H−ピラゾール−5−カルボキサミド、および、
N2−[1,1−ジメチル−2−(メチルスルホニル)エチル]−3−ヨード−N1−[2−メチル−4−[1,2,2,2−テトラフルオロ−1−(トリフルオロメチル)エチル]フェニル]−1,2−ベンゼンジカルボキサミド。
実施例A〜Eおよび比較例A〜Eにおいて、以下の一般的な方法を用いた。表1に、それらの成分の化学的な名称を列挙し、表2Aおよび2Bに、実施例A〜Eおよび比較例A〜Eの組成物中で用いられる量を列挙した。オーバヘッド撹拌器を備えた250mLのステンレス鋼ビーカー中に、液体担体、カルボキサミド節足動物駆除物質、乳化剤、およびその他の成分(各実施例ごとに特定されたもの)を撹拌しながら混合し、100gの混合物にした。この混合物を、ローターステーターミキサー(ポリトロン(Polytron)PT3000,キネマティカ社(Kinematica AG),スイス)を用いてホモジナイズし、次に、50mLのアイガー・モーターミル(Eiger Motormill)(アイガー・マシーナリー社(Eiger Machinery Inc.)、イリノイ州シカゴによって製造された水平型のビーズミル)を用いて約1ミクロンの適度な粒度に磨砕し、懸濁液濃縮物を得た。
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミドの製造
アセトニトリル(114kg)中の3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボン酸(20.6kg)、および、2−アミノ−5−シアノ−N,3−ジメチルベンズアミド(14.1kg)の混合物に、3−ピコリン(22.2kg)を添加した。この混合物を−10〜−14℃に冷却し、次に、塩化メタンスルホニル(10.6kg)を、温度が5℃を超えないようにゆっくり添加した。HPLCおよびNMR解析によって反応が完了したことが確認されたら、この混合物を、水(72.6kg)および濃塩酸(7.94kg)を、温度が5℃を超えないような速度で連続的に添加することによって後処理した。5℃を超えない温度で約30分間維持した後、反応混合物をろ過して、固体生成物を回収し、これをアセトニトリル−水(2:1、2×12.3kg)、および、アセトニトリル(2×10.4kg)で連続的に洗浄した。次に、この固体を、約50℃、減圧下および窒素ガスのフロー下で乾燥させ、表題の生成物を白色の結晶性固体として得て、これを本発明の調合物の実施例および比較例で直接用いた。適度な加熱速度(5分間にわたり約150℃に加熱し、次に、加熱速度を約4〜5℃/分から約3℃/分に減少させ、約15分間以上かけて210℃に到達させた)を用いて、緩く取り込まれた溶媒を固体生成物から容易に揮発させ、204〜210℃の範囲で溶融を起こした。
各実施例の化学的安定性を、サンプルを加熱したオーブン中で(すなわち54℃で2週間)熟成させ、次に熟成の前後でカルボキサミド節足動物駆除物質の含量を比較することによって評価した。カルボキサミド節足動物駆除物質含量を、逆相カラムを用いた高圧液体クロマトグラフィー(HPLC)で組成物を分析することによって決定した。カルボキサミド節足動物駆除物質の最終的な質量パーセントをカルボキサミド節足動物駆除物質の最初の質量パーセントから引き、その差をカルボキサミド節足動物駆除物質の最初の質量パーセントで割り、得られた商に100(%)を掛けることによって、相対的な分解のパーセントを計算した。
試験A
接触および/または全体的な手段によってウェスタン・フラワー・トリップ(アザミウマ)(Frankliniella occidentalis Pergande)の防除を評価するために、各試験単位を、少なくとも2枚の本葉を有するマメ科の植物(var.Soleil)で構成し、これをレジ−アース(Redi−earth(R))培地(スコッツ社(Scotts Co.))で栽培した。1つの植物は1回の反復実験とみなした;1回の処理ごとに4回の反復実験を用いた。
シルバーリーフコナジラミ(silverleaf whitefly)(Bemisia argentifolii Bellows&Perring)の防除を評価するために、試験単位を、少なくとも2枚の本葉を有する14〜21日齢のコットンプラントで構成し、これをレジ−アース(R)培地(スコッツ社)で栽培した。この植物を遮蔽したケージ中に置き、ここにコナジラミ成虫を導入し、約20〜4時間で産卵させた。産卵が観察された植物だけを試験に用いた。試験溶液を噴霧する前に、植物を卵の孵化と幼虫の定住に関して再度チェックした。植物あたり1枚の葉を1回の反復実験とみなした;1回の処理ごとに4回の反復実験を用いた。
接触および/または全体的な手段によってモモアカアブラムシ(Myzus persicae)の防除を評価するために、試験単位を、試験溶液での処理の24時間前に前もって30〜40匹のアブラムシを付着させた3週齢のラディッシュ植物で構成した。1つの植物を1回の反復実験とみなし、1回の処理ごとに4回の反復実験を用いた。
シロイチモンジヨトウガの幼虫(Spodoptera exigua)の防除に関して耐雨性(洗い流しに対する耐性)を評価するために、試験単位を、レジ−アース(R)培地を含む鉢で成長させたコットンプラントで構成した。試験溶液を試験Aで説明されているようにして配合した。植物が4〜6枚の本葉が成長した段階になったら、植物に、植物より19cm上に位置するノズルを有するベルト噴霧器を用いて配合された試験溶液を噴霧した(234リットル/haの適用体積が提供された)。配合された試験溶液の噴霧後に、各試験単位を2時間乾燥させ、次に、温室中で約95mmの擬似雨に晒した。次に、植物を乾燥させ、葉を切断し、16セルのプラスチックトレイ中で寒天上に置いた。1セルあたり1匹の3日齢の実験室で飼育したシロイチモンジヨトウガの幼虫を置き、セルをプラスチックの蓋で覆った。1回の処理ごとに2つの16セルトレイを用いた。トレイを、培養室で、75%の相対湿度で、明所で16時間(昼間として)、および、暗所、25℃で8時間(夜間として)で保持した。付着させてから4日後に、各試験単位を幼虫の死亡率に関して評価し、個体群の50%を死滅させる平均濃度(平均LC50)を計算し、それを表4Dに列挙した。
シルバーリーフコナジラミ(Bemisia argentifolii)の防除に関して、本発明の組成物のアジュバントとしてのメチル化された種油の作用を評価するために、試験単位を、少なくとも2枚の本葉を有する14〜21日齢のコットンプラントで構成し、これをレジ−アース(R)培地(スコッツ社)で栽培した。この植物を遮蔽したケージ中に置き、ここにコナジラミ成虫を導入し、約20〜4時間で産卵させた。産卵が観察された植物だけを試験に用いた。試験溶液を噴霧する前に、植物を卵の孵化と幼虫の定住に関して再度チェックした。植物あたり1枚の葉を1回の反復実験とみなした;1回の処理ごとに4回の反復実験を用いた。
Claims (8)
- 節足動物を駆除するための懸濁液濃縮組成物であって、該組成物の総質量に基づく質量で、
(a)0.1〜40%の少なくとも1つの室温で固体のカルボキサミド節足動物駆除物質;
(b)0〜20%の少なくとも1つのその他の生物活性物質;
(c)30〜95%の少なくとも1つの水不混和性の液体担体;
(d)0〜50%の少なくとも1つの乳化剤;
(e)0.01〜10%のシリカ増粘剤;
(f)0.1〜10%の、水、C1〜C12アルカノール、および、C2〜C3グリコールから選択される少なくとも1つのプロトン性溶媒;および、
(g)0.001〜5%の少なくとも1つの水溶性カルボン酸、
を含む、上記組成物。 - 構成要素(a)は、組成物の5〜25質量%であり;構成要素(b)は、組成物の0〜15質量%であり;構成要素(c)は、C1〜C4アルカノールの脂肪酸エステル、アルコキシル化脂肪酸エステル、植物油、および、鉱油からなる群より選択される少なくとも1つの物質を含み、そして、組成物の40〜70質量%であり;構成要素(d)は、アニオン性界面活性剤、非イオン界面活性剤、および、これらの混合物から選択され、そして、組成物の10〜40質量%であり;構成要素(e)は、組成物の0.01〜5質量%であり;構成要素(f)は、組成物の0.5〜5質量%であり;そして、構成要素(g)は、組成物の0.01〜5質量%である、請求項1〜3のいずれか一項に記載の組成物。
- 構成要素(c)は、C1〜C2アルカノールの飽和または不飽和C16〜C18脂肪酸エステルを含み、そして、組成物の50〜60質量%であり;構成要素(d)は、アニオン性界面活性剤、および、非イオン界面活性剤の混合物を含み、ここにおいて該アニオン性界面
活性剤の該非イオン界面活性剤に対する比率は、2:1〜1:10の範囲であり;構成要素(e)は、ヒュームドシリカを含み;構成要素(f)は、水を含み、この水は、組成物の0.5〜5質量%であり;そして、構成要素(g)は、クエン酸を含み、そして該クエン酸は、組成物の0.01〜2質量%である、請求項4に記載の組成物。 - 構成要素(c)は、ヒマワリ、ダイズ、綿またはリンシードのメチル化種油を含む、請求項4に記載の組成物。
- アニオン性界面活性剤は、直鎖アルキルベンゼンスルホン酸塩であり、非イオン界面活性剤は、エトキシ化ソルビトールエステル、エトキシ化ソルビタンエステル、エトキシ化脂肪酸エステル、および、それらの混合物から選択され、該アニオン性界面活性剤の該非イオン界面活性剤に対する比率は、質量で2:1〜1:5の範囲である、請求項4に記載の組成物。
- 少なくとも1つのその他の生物活性物質は、アバメクチン、アセタミプリド、アミトラズ、エバーメクチン、アザジラクチン、ビフェントリン、ブプロフェジン、カルタップ、クロルフェナピル、クロルピリホス、クロチアニジン、シフルトリン、ベータ−シフルトリン、シハロトリン、ラムダ−シハロトリン、シペルメトリン、シロマジン、デルタメトリン、ジエルドリン、ジノテフラン、ジオフェノラン、エマメクチン、エンドスルファン、エスフェンバレレート、エチプロール、フェノチオカルブ、フェノキシカルブ、フェンバレラート、フィプロニル、フロニカミド、フルフェノクスロン、ヘキサフルムロン、ヒドラメチルノン、イミダクロプリド、インドキサカルブ、ルフェヌロン、メタフルミゾン、メトミル、メトプレン、メトキシフェノジド、ニテンピラム、ニチアジン、ノバルロン、オキサミル、ピメトロジン、ピレトリン、ピリダベン、ピリダリル、ピリプロキシフェン、リアノジン、スピネトラム、スピノサド、スピロジクロフェン、スピロメシフェン、テブフェノジド、チアクロプリド、チアメトキサム、チオジカルブ、チオスルタップ−ナトリウム、トラロメトリン、トリアザメート、トリフルムロン、バチルス・チューリンゲンシス サブスピーシズ アイザワイ、バチルス・チューリンゲンシス サブスピーシズ クルスターキ、核多角体病ウイルス、および、バチルス・チューリンゲンシスのカプセル封入されたδ−内毒素から選択される、請求項1に記載の組成物。
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